Curable composition, film, cured product, and medical member

ABSTRACT

A curable composition contains a betaine monomer having a predetermined structure and a polyfunctional (meth)acrylamide compound having a predetermined structure.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application is a Continuation of PCT International Application No.PCT/JP2018/037662 filed on Oct. 10, 2018, which claims priority under 35U.S.C § 119(a) to Japanese Patent Application No. 2017-201962 filed onOct. 18, 2017. Each of the above application(s) is hereby expresslyincorporated by reference, in its entirety, into the presentapplication.

BACKGROUND OF THE INVENTION 1. Field of the Invention

The present invention relates to a curable composition, a film, a curedproduct, and a medical member.

2. Description of the Related Art

Originally, it is desired that artificial organs, medical instruments,and the like are made of a material which is compatible with a substanceconstituting a living body and is hardly contaminated. For example, itis desired that artificial blood vessels, catheters, stents, artificialbones, and dentures that are introduced into a human body for a longperiod of time do not cause an inflammatory response and rejection. Inaddition, the replacement of those artificial organs or medicalinstruments caused by contamination imposes a burden on the patient.Therefore, it is desired that artificial organs, medical instruments,and the like are formed of a material which hardly interacts withbiological materials such as proteins, blood cells, and cells. That is,it is desired that artificial organs, medical instruments, and the likeare formed of a material difficult for the aforementioned biologicalmaterials to be attached (adhere).

For example, WO2016/067795A discloses “a material nonadhesive tobiological materials containing a polymer compound (A) containing arepeating unit derived from a sulfobetaine monomer having apredetermined structure”. Examples in WO2016/067795A specificallydisclose a curable composition containing a sulfobetaine monomer havingthe aforementioned predetermined structure and a (meth)acrylate-basedmonomer or N-[tris(3-acrylamidopropoxymethyl)methyl] acrylamide as acrosslinking agent and a cured product of the curable composition(material nonadhesive to biological materials).

SUMMARY OF THE INVENTION

The cured product (material nonadhesive to biological materials) is alsorequired to have excellent substrate adhesion. In the living body,artificial organs, medical instruments, and the like are generally usedin a situation where these contact body fluids (for example, saliva,blood, and the like), which contain water as a main component, with highfrequency. Therefore, “have excellent substrate adhesion” mentionedherein means that even after a substrate with a film, which includes asubstrate and a film formed on the substrate, is immersed in an aqueousliquid, the film is not peeled or hardly peeled from the substrate.Examples of the substrate include medical instruments such as artificialblood vessels, catheters, stents, artificial bones, and dentures.

The inventors of the present invention prepared the curable compositiondescribed in Examples in WO2016/067795A and examined the physicalproperties of the cured product. As a result, it has been revealed thatthe cured product does not necessarily satisfy the currently requiredlevel of substrate adhesion, and needs to be further improved.

Therefore, an object of the present invention is to provide a curablecomposition capable of providing a cured product having excellentsubstrate adhesion and excellent biocompatibility.

Another object of the present invention is to provide a cured productand a film having excellent substrate adhesion and excellentbiocompatibility.

Another object of the present invention is to provide a medical membercomprising the cured product.

In order to achieve the above objects, the inventors of the presentinvention conducted intensive studies. As a result, the inventors havefound that the above objects can be achieved in a case where the curablecomposition contains a betaine monomer having a predetermined structureand a predetermined polyfunctional (meth)acrylamide compound, and haveaccomplished the present invention.

That is, the inventors have found that the above objects can be achievedby the following constitution.

[1] A curable composition containing one or more betaine monomersselected from the group consisting of a compound represented by Formula(1) which will be described later and a compound represented by Formula(2) which will be described later, and one or more polyfunctionalcompounds selected from the group consisting of a compound representedby Formula (A1) which will be described later and a compound representedby Formula (A2) which will be described later.

[2] The curable composition described in [1], in which A¹ in Formula (1)represents S═O, and A² in Formula (2) represents S═O.

[3] A film containing a polymer compound containing one or morerepeating units selected from the group consisting of a repeating unitderived from a compound represented by Formula (1) which will bedescribed later and a repeating unit derived from a compound representedby Formula (2) which will be described later, and one or more repeatingunits selected from the group consisting of a repeating unit derivedfrom a compound represented by formula (A1) which will be describedlater and a repeating unit derived from a compound represented byFormula (A2) which will be described later.

[4] A cured product formed by curing the curable composition describedin [1] or [2].

[5] The cured product described in [4] that is in the form of a film.

[6] The cured product described in [4] or [5] that is used as abiomaterial.

[7] A medical member containing a substrate and the cured productdescribed in any one of [4] to [6] disposed on the substrate.

According to the present invention, it is possible to provide a curablecomposition capable of providing a cured product having excellentsubstrate adhesion and excellent biocompatibility.

Furthermore, according to the present invention, it is possible toprovide a cured product and a film having excellent substrate adhesionand excellent biocompatibility.

In addition, according to the present invention, it is possible toprovide a medical member comprising the cured product.

DESCRIPTION OF THE PREFERRED EMBODIMENTS

Hereinafter, the present invention will be specifically described.

The following constituents will be described based on the typicalembodiments of the present invention in some cases, but the presentinvention is not limited to the embodiments.

In the present specification, a range of numerical values describedusing “to” means a range including numerical values listed before andafter “to” as a lower limit and an upper limit.

In the present specification, “(meth)acrylamide” has a concept includingeither or both of the acrylamide and methacrylamide. The same is true ofthe terms such as “(meth)acryl”, “(meth)acrylate”, and “(meth)acryloyl”.

In the present specification, in a case where there is a plurality ofsubstituents, linking groups, and the like (hereinafter, described assubstituents and the like) marked with specific reference signs, or in acase where a plurality of substituents and the like are simultaneouslyspecified, the substituents and the like may be the same as or differentfrom each other. The same is true of a case where the number ofsubstituents and the like is specified.

Furthermore, in the present specification, in a case where there is nodescription regarding whether or not a group (atomic group) issubstituted or unsubstituted, the group includes both the group havingno substituent and group having a substituent. For example, “alkylgroup” includes not only an alkyl group having no substituent(unsubstituted alkyl group) but also an alkyl group having a substituent(substituted alkyl group).

In the present specification, “biological material” is a term that meansa wide variety of materials including materials constituting the livingbody and materials involved in the living body. For example, the termmeans materials including proteins, cells, tissues which is a group ofcells, peptides, vitamins, hormones, blood cells, antigens, antibodies,bacteria, viruses, and the like.

Furthermore, in the present specification, the term “properties ofinhibiting the adhesion of biological materials” means the properties ofperfectly preventing adhesion and also suppressing adhesion (reducingadhesion) before and after application even though adhesion occurs.Therefore, the term has a concept including not only the prevention ofadhesion but also the inhibition of adhesion.

[Curable Composition]

One of the characteristics of the curable composition according to anembodiment of the present invention (hereinafter, referred to as “thecomposition according to the embodiment of the present invention” aswell) contains one or more betaine monomers (hereinafter, referred to as“specific betaine monomer” as well) selected from the group consistingof a compound represented by Formula (1) which will be described laterand a compound represented by Formula (2) which will be described later,and one or more polyfunctional compounds (hereinafter, referred to as“specific polyfunctional (meth)acrylamide compound” as well) selectedfrom the group consisting of a compound represented by Formula (A1) anda compound represented by Formula (A2) which will be described later.

The inventors of the present inventions have revealed that a curedproduct formed of the curable composition described above areparticularly excellent in both the substrate adhesion andbiocompatibility. More specifically, due to the structuralcharacteristics, the specific betaine monomer forms a film having highcrosslinking density together with the specific polyfunctional(meth)acrylamide compound described above. Presumably, as a result, evenin a case where a substrate with a film, which includes a substrate anda film formed on the substrate, is immersed in an aqueous liquid, theaqueous liquid may be inhibited from permeating the interface betweenthe substrate and the film.

The specific betaine monomer exhibits excellent biocompatibility due toa betaine moiety in the compound.

Hereinafter, each of the components contained in the composition of thepresent invention will be specifically described.

[Specific Betaine Monomer]

The composition according to the embodiment of the present inventioncontains one or more betaine monomers selected from the group consistingof a compound represented by Formula (1) and a compound represented byFormula (2). Generally, betaine refers to a compound (inner salt) whichhas a positive charge and a negative charge at non-adjacent positions inthe same molecule but does not carry a charge as a whole molecule, inwhich a hydrogen atom is not bonded to an atom having a positive charge.

In Formula (1), R¹ represents a hydrogen atom or an alkyl group.

The number of carbon atoms in the alkyl group represented by R¹ is notparticularly limited, but is preferably 1 to 15, more preferably 1 to10, even more preferably 1 to 6, and particularly preferably 1 to 3. Thealkyl group may be linear, branched, or cyclic.

Examples of the alkyl group include a methyl group, an ethyl group, an-propyl group, an isopropyl group, a n-butyl group, a t-butyl group, an-hexyl group, a cyclopentyl group, a cyclohexyl group, and the like.

The alkyl group may have a substituent. The substituent that the alkylgroup can have is not particularly limited, and examples thereof includea substituent W which will be described later.

As R¹, particularly, a hydrogen atom or an alkyl group having 1 to 6carbon atoms is preferable, and a hydrogen atom or an alkyl group having1 to 3 carbon atoms is more preferable.

R² and R³ each independently represent an alkyl group.

The alkyl group represented by R² and R³ has the same definition as thealkyl group represented by R¹, and the suitable embodiments thereof arealso the same.

R^(1A) represents an oxygen atom or NR¹⁰¹.

R¹⁰¹ represents a hydrogen atom or an alkyl group. The alkyl grouprepresented by R¹⁰¹ has the same definition as the alkyl grouprepresented by R¹, and the suitable embodiments thereof are also thesame. As R¹⁰¹, a hydrogen atom is preferable.

a represents an integer of 2 to 6.

In view of further improving the substrate adhesion, a is preferably 2to 4, and more preferably 2 or 3.

L¹ represents an (a+1)-valent aliphatic hydrocarbon group which maycontain —O—, —NR¹⁰²—, —CO— (corresponding to —C(═O)—), or a divalentlinking group obtained by combining these. That is, L¹ is linked to apieces of monovalent group represented by Formula (X) and a nitrogenatom (cationized nitrogen atom) specified in Formula (1).

In Formula (X), R¹ and R^(1A) have the same definitions as R¹ and R^(1A)in Formula (1).*represents a position linked to L¹.

R¹⁰² represents a hydrogen atom or a substituent. The substituentrepresented by R¹⁰² is not particularly limited, and examples thereofinclude the substituent W which will be described later. As R¹⁰², ahydrogen atom is particularly preferable.

The number of carbon atoms in the aliphatic hydrocarbon grouprepresented by L¹ is not particularly limited, but is, for example, 1 to30, preferably 1 to 20, more preferably 1 to 15, even more preferably 1to 12, and particularly preferably 3 to 12. The aliphatic hydrocarbongroup represented by L¹ may be linear, branched, or cyclic.

Furthermore, the aliphatic hydrocarbon group may have a substituent. Thesubstituent that the aliphatic hydrocarbon group can have is notparticularly limited, and examples thereof include a substituent W whichwill be described later.

In L¹, a carbon atom is usually located at a position adjacent to anitrogen atom (cationized nitrogen atom) specified in the chemicalformula and at a position adjacent to R^(1A).

Examples of L¹, include a linking group represented by Formula (1A-1) ora linking group represented by Formula (1A-2).

In Formula (1A-1), R¹⁰³ represents a hydrogen atom or a substituent. Thesubstituent is not particularly limited, and examples thereof includethe substituent W which will be described later.

In Formulas (1A-1) and (1A-2), L¹⁰¹ to L¹⁰⁷ each represent a single bondor an alkylene group which may contain —O—, —NR¹⁰²—, —CO—, or a divalentlinking group obtained by combining these. R¹⁰² is as described above.

The number of carbon atoms in the alkylene group, which is representedby L¹⁰¹ to L¹⁰⁷ and may contain —O—, —NR¹⁰⁴—, —CO—, or a divalentlinking group obtained by combining these, is not particularly limited.For example, the number of carbon atoms in the alkylene group ispreferably 1 to 12, more preferably 1 to 6, and even more preferably 2to 6. Q* represents a position linked to the monovalent grouprepresented by Formula (X), and * represents a position linked to anitrogen atom (cationized nitrogen atom) specified in Formula (1).

L¹⁰¹ to L¹⁰⁷ may further have a substituent. The substituent is notparticularly limited, and examples thereof include the substituent Wwhich will be described later. In L¹⁰¹ to L¹⁰⁷, a carbon atom is usuallylocated at a position linked to Q*.

L² represents an alkylene group which may contain —O—, —NR¹⁰²—, —CO—, ora divalent linking group obtained by combining these. R¹⁰² is asdescribed above.

The number of carbon atoms in the alkylene group, which is representedby L² and may contain —O—, —NR¹⁰²—, —CO—, or a divalent linking groupobtained by combining these, is not particularly limited. For example,the number of carbon atoms in the alkylene group is 1 to 30, preferably1 to 20, more preferably 1 to 15, and even more preferably 1 to 12.

In L², a carbon atom is usually located at a position adjacent to anitrogen atom (cationized nitrogen atom) specified in the chemicalformula.

Furthermore, the alkylene group may have a substituent. The substituentthat the alkylene group, which is represented by L² and may contain —O—,—NR¹⁰²—, —CO—, or a divalent linking group obtained by combining these,is not particularly limited, and examples of the substituent include thesubstituent W which will be described later.

A¹ represents S═O or a carbon atom. In view of further improving thebiocompatibility, A¹ is preferably S═O.

In Formula (2), R⁴ and R⁶ each independently represent a hydrogen atomor an alkyl group. The alkyl group represented by R⁴ and R⁶ has the samedefinition as the alkyl group represented by R¹ in Formula (1), and thesuitable embodiments thereof are also the same. As R⁴ and R⁶,particularly, a hydrogen atom or an alkyl group having 1 to 6 carbonatoms is preferable, and a hydrogen atom or an alkyl group having 1 to 3carbon atoms is more preferable.

R⁵ represents an alkyl group. The alkyl group represented by R⁵ has thesame definition as the alkyl group represented by R² and R³ in Formula(1), and the suitable embodiments thereof are also the same.

R^(1B) and R^(1C) each independently represent an oxygen atom or NR¹⁰³.R¹⁰³ represents a hydrogen atom or an alkyl group. The alkyl grouprepresented by R¹⁰³ has the same definition as the alkyl grouprepresented by R¹⁰¹ in Formula (1), and the suitable embodiments thereofare also the same. As R¹⁰³, a hydrogen atom is preferable.

b and c each independently represent an integer of 1 to 5. However, band c satisfy 2≤b+c≤6.

In view of further improving the substrate adhesion, b+c is preferably 2to 4, and more preferably 2 or 3. b is preferably 1 to 3, and morepreferably 1. Furthermore, c is preferably 1 to 3, and more preferably1.

L³ represents a (b+1)-valent aliphatic hydrocarbon group which maycontain —O—, —NR¹⁰⁴—, —CO—, or a divalent linking group obtained bycombining these. That is, L³ is linked to b pieces of monovalent grouprepresented by Formula (Y) and a nitrogen atom (cationized nitrogenatom) specified in Formula (2).

In Formula (Y), R⁴ and R^(1B) have the same definitions as R⁴ and R^(1B)in Formula (2). * represents a position linked to L³.

R¹⁰⁴ represents a hydrogen atom or a substituent. The substituentrepresented by R¹⁰⁴ is not particularly limited, and examples thereofinclude the substituent W which will be described later. Among these, ahydrogen atom is preferable as R¹⁰⁴.

The number of carbon atoms in the aliphatic hydrocarbon grouprepresented by L³ is not particularly limited, but is, for example, 1 to30, preferably 1 to 20, more preferably 1 to 15, even more preferably 1to 12, and particularly preferably 3 to 12. The aliphatic hydrocarbongroup represented by L³ may be linear, branched, or cyclic.

Furthermore, the aliphatic hydrocarbon group may have a substituent. Thesubstituent that the aliphatic hydrocarbon group can have is notparticularly limited, and examples thereof include a substituent W whichwill be described later.

In L³, a carbon atom is usually located at a position adjacent to anitrogen atom (cationized nitrogen atom) specified in the chemicalformula and at a position adjacent to R^(1B).

Examples of L³ include a linking group represented by Formula (2A-1), alinking group represented by Formula (2A-2), and a linking grouprepresented by Formula (2A-3).

In Formulas (2A-1) and (2A-2), R²⁰¹ to R²⁰³ each represent a hydrogenatom or a substituent. The substituent is not particularly limited, andexamples thereof include the substituent W which will be describedlater.

In Formulas (2A-1) to (2A-3), L²⁰¹ to L²⁰⁹ each represent a single bondor an alkylene group which may contain —O—, —NR¹⁰⁴—, —CO—, or a divalentlinking group obtained by combining these. R¹⁰⁴ is as described above.

The number of carbon atoms in the alkylene group, which is representedby L²⁰¹ to L²⁰⁹ and may contain —O—, —NR¹⁰⁴—, —CO—, or a divalentlinking group obtained by combining these, is not particularly limited.For example, the number of carbon atoms in the alkylene group ispreferably 1 to 12, more preferably 1 to 6, and even more preferably 2to 6. P* represents a position linked to the monovalent grouprepresented by Formula (Y), and * represents a position linked to anitrogen atom (cationized nitrogen atom) specified in Formula (2).

L²⁰¹ to L²⁰⁹ may further have a substituent. The substituent is notparticularly limited, and examples thereof include the substituent Wwhich will be described later. In L²⁰¹ to L²⁰⁹, a carbon atom is usuallylocated at a position linked to P*.

L⁴ represents a (c+1)-valent aliphatic hydrocarbon group which maycontain —O—, —NR¹⁰⁴—, —CO—, or a divalent linking group obtained bycombining these. That is, L⁴ is linked to c pieces of monovalent grouprepresented by Formula (Z) and a nitrogen atom (cationized nitrogenatom) specified in Formula (2).

In Formula (Z), R⁶ and R^(1C) have the same definitions as R⁶ and R^(1C)in Formula (2). * represents a position linked to L⁴.

R¹⁰⁴ is as described above.

The number of carbon atoms in the aliphatic hydrocarbon grouprepresented by L⁴ is not particularly limited, but is, for example, 1 to30, preferably 1 to 20, more preferably 1 to 15, even more preferably 1to 12, and particularly preferably 3 to 12. The aliphatic hydrocarbongroup represented by L⁴ may be linear, branched, or cyclic.

Furthermore, the aliphatic hydrocarbon group may have a substituent. Thesubstituent that the aliphatic hydrocarbon group can have is notparticularly limited, and examples thereof include a substituent W whichwill be described later.

In L⁴, a carbon atom is usually located at a position adjacent to anitrogen atom (cationized nitrogen atom) specified in the chemicalformula and at a position adjacent to R^(1C).

Examples of L⁴ include a linking group represented by Formula (3A-1), alinking group represented by Formula (3A-2), and a linking grouprepresented by Formula (3A-3).

In Formulas (3A-1) and (3A-2), R³⁰¹ to R³⁰³ each represent a hydrogenatom or a substituent. The substituent is not particularly limited, andexamples thereof include the substituent W which will be describedlater.

In Formulas (3A-1) to (3A-3), L³⁰¹ to L³⁰⁹ each represent a single bondor an alkylene group which may contain —O—, —NR¹⁰⁴—, —CO—, or a divalentlinking group obtained by combining these. R¹⁰⁴ is as described above.

The number of carbon atoms in the alkylene group, which is representedby L³⁰¹ to L³⁰⁹ and may contain —O—, —NR¹⁰⁴—, —CO—, or a divalentlinking group obtained by combining these, is not particularly limited.For example, the number of carbon atoms in the alkylene group ispreferably 1 to 12, more preferably 1 to 6, and even more preferably 2to 6. W* represents a position linked to the monovalent grouprepresented by Formula (Z), and * represents a position linked to anitrogen atom (cationized nitrogen atom) specified in Formula (2).

L³⁰¹ to L³⁰⁹ may further have a substituent. The substituent is notparticularly limited, and examples thereof include the substituent Wwhich will be described later. In L³⁰¹ to L³⁰⁹, a carbon atom is usuallylocated at a position linked to P*.

In Formula (2), the total number of P* in L³ and W* in L⁴ is 2 to 6.

L⁵ represents an alkylene group which may contain —O—, —NR¹⁰⁴—, —CO—, ora divalent linking group obtained by combining these. R¹⁰⁴ is asdescribed above.

The number of carbon atoms in the alkylene group, which is representedby L⁵ and may contain —O—, —NR¹⁰⁴—, —CO— or a divalent linking groupobtained by combining these, is not particularly limited. For example,the number of carbon atoms in the alkylene group is 1 to 30, preferably1 to 20, more preferably 1 to 15, and even more preferably 1 to 12.

In L⁵, a carbon atom is usually located at a position adjacent to anitrogen atom (cationized nitrogen atom) specified in the chemicalformula.

Furthermore, the alkylene group may have a substituent. The substituentthat the alkylene group, which is represented by L⁵ and may contain —O—,—NR¹⁰²—, —CO—, or a divalent linking group obtained by combining these,can have is not particularly limited, and examples of the substituentinclude the substituent W which will be described later.

A² represents S═O or a carbon atom. In view of further improving thebiocompatibility, A² is preferably S═O.

The specific betaine monomer can be synthesized according to a knownmethod.

One kind of the specific betaine monomer may be used singly, or two ormore kinds of the specific betaine monomers may be used in combination.

In the composition according to the embodiment of the present invention,the content of the betaine monomer (total content in a case where thecomposition contains a plurality of kinds of the betaine monomers) withrespect to the total solid content of the composition is preferably 10%to 99% by mass, more preferably 20% to 85% by mass, and even morepreferably 30% to 70% by mass.

In the present specification, “solid content” means componentsconstituting a cured product and does not include a solvent. A monomeris a component constituting the cured product. Therefore, the monomer isincluded in the solid content even if the monomer is a liquid.

Specific examples of the specific betaine monomer will be shown below,but the present invention is not limited thereto.

[Specific Polyfunctional (Meth)Acrylamide Compound]

The composition according to the embodiment of the present inventioncontains one or more specific polyfunctional (meth)acrylamide compoundsselected from the group consisting of a compound represented by Formula(A1) which will be described later and a compound represented by Formula(A2) which will be described later.

Hereinafter, the specific polyfunctional (meth)acrylamide compound willbe described.

Compound represented by formula (A1)

In Formula (A1), R²⁰ each independently represents a hydrogen atom or amethyl group, a plurality of R²⁰s may be the same as or different fromeach other.

L²⁰ each independently represents —O—, an alkylene group having 2 to 4carbon atoms, or a divalent linking group obtained by combining these.In L²⁰, it is preferable that a carbon atom is located at a positionadjacent to a nitrogen atom in the amide group specified in the chemicalformula. That is, as the group adjacent to a nitrogen atom in the amidegroup, an alkylene group having 2 to 4 carbon atoms is preferablylocated at the aforementioned position.

Examples of the aforementioned “divalent linking group obtained bycombining these” include an alkylene group having 2 to 4 carbon atomscontaining —O—, such as —OCH₂CH₂—, —OCH₂CH₂CH₂—, —OCH₂CH₂CH₂CH₂—,—CH₂OCH₂—, —CH₂OCH₂CH₂—, or —CH₂OCH₂CH₂CH₂— and a group represented by—(O-alkylene group (having 2 to 4 carbon atoms))_(n)—, and the like.Herein, n represents an integer of 2 or greater. The upper limit of n isnot particularly limited, but is, for example, about 10.

In each of the groups exemplified as “divalent linking group obtained bycombining these”, any of the two binding sites may be bonded to theamide group.

Particularly, in view of further improving the substrate adhesion andthe biocompatibility, L²⁰ is preferably an alkylene group having 2 to 4carbon atoms containing —O—.

Furthermore, a plurality of L²⁰s may be the same as or different fromeach other.

Compound represented by Formula (A2)

In Formula (A2), R²⁰ each independently represents a hydrogen atom or amethyl group.

R²¹ and R²³ each independently represent —O—, an alkylene group having 1to 4 carbon atoms, or a divalent linking group obtained by combiningthese. In R²¹ and R²³, it is preferable that a carbon atom is usuallylocated at a position adjacent to a nitrogen atom in the amide groupspecified in the chemical formula. As the group adjacent to a nitrogenatom in the amide group, an alkylene group having 1 to 4 carbon atoms ispreferably located at the aforementioned position.

Examples of the “divalent linking group obtained by combining these”include an alkylene group having 1 to 4 carbon atoms containing —O—,such as —OCH₂—, —OCH₂CH₂—, —OCH₂CH₂CH₂—, —OCH₂CH₂CH₂CH₂—, —CH₂OCH₂—,—CH₂OCH₂CH₂—, or —CH₂OCH₂CH₂CH₂—, and a group represented by—(O-alkylene group (having 1 to 4 carbon atoms))_(n)—. Herein, nrepresents an integer of 2 or greater. The upper limit of n is notparticularly limited, but is, for example, about 10.

In each of the groups exemplified as “divalent linking group obtained bycombining these”, any of the two binding sites may be bonded to theamide group.

Particularly, in view of further improving the substrate adhesion andthe biocompatibility, R²¹ and R²³ more preferably each independentlyrepresent an alkylene group having 1 to 4 carbon atoms or an alkylenegroup having 1 to 4 carbon atoms containing —O—, and even morepreferably each independently represent an alkylene group having 1 to 4carbon atoms containing —O—.

In Formula (A2), R²² represents —O—, an alkylene group having 1 to 4carbon atoms, a group represented by Formula (B), or a divalent linkinggroup obtained by combining these.

Examples of the “divalent linking group combining these” include thegroups described above for R²¹ and R²³. In a case where the grouprepresented by Formula (B) is combined with another group, it ispreferable that an alkylene group having 1 to 4 carbon atoms is bondedto a nitrogen atom in the group represented by Formula (B).

Particularly, in view of further improving the substrate adhesion andthe biocompatibility, R²² more preferably represents an alkylene grouphaving 1 to 4 carbon atoms, an alkylene group having 1 to 4 carbon atomscontaining —O—, or a group represented by Formula (B), and even morepreferably represents an alkylene group having 1 to 4 carbon atomscontaining —O—.

L²¹ and L²² each independently represent a single bond or a grouprepresented by Formula (B).

In a case where R²² represents Formula (B), it is preferable that boththe L²¹ and L²² represent a single bond.

In Formula (B), * represents a binding position.

In Formula (B), R²⁰ represents a hydrogen atom or a methyl group, and *represents a linking position. Usually, a carbon atom is located at *.

In view of further improving the biocompatibility, the compoundrepresented by Formula (A2) described above is preferably a compoundrepresented by Formula (A3).

R²⁰ in Formula (A3) has the same definition as R²⁰ in Formula (A1), andthe suitable embodiments thereof are also the same. R^(21a), R^(22a),and R^(23a) each independently represent an alkylene group having 1 to 4carbon atoms containing —O—. Specifically, examples thereof include—OCH₂—, —OCH₂CH₂—, —OCH₂CH₂CH₂—, —OCH₂CH₂CH₂CH₂—, —CH₂OCH₂—,—CH₂OCH₂CH₂—, —CH₂OCH₂CH₂CH₂—, —CH₂CH₂OCH₂CH₂—, and the like.

Specific examples of the specific polyfunctional (meth)acrylamidecompound will be shown below, but the present invention is not limitedthereto.

As the specific polyfunctional (meth)acrylamide compound, variouscommercially available products can be used. Alternatively, the specificpolyfunctional (meth) acrylamide compound can be synthesized by themethod described in Journal of Technical Disclosure No. 2013-502654.

One kind of the specific polyfunctional (meth) acrylamide compound maybe used singly, or two or more kinds of the specific polyfunctional(meth)acrylamide compounds may be used in combination.

In the composition according to the embodiment of the present invention,the content of the specific polyfunctional (meth)acrylamide compound(total content in a case where the composition contains a plurality ofkinds of the specific polyfunctional (meth)acrylamide compounds) withrespect to the total solid content of the composition is preferably 5%to 80% by mass, more preferably 10% to 60% by mass, and even morepreferably 10% to 55 mass %.

(Substituent Group W)

Examples of the substituent W includes an alkyl group (preferably analkyl group having 1 to 20 carbon atoms), an alkenyl group (preferablyan alkenyl group having 2 to 20 carbon atoms), an alkynyl group(preferably an alkynyl group having 2 to 20 carbon atoms), a cycloalkylgroup (preferably a cycloalkyl group having 3 to 20 carbon atoms), anaryl group (preferably an aryl group having 6 to 26 carbon atoms), aheterocyclic group (preferably a heterocyclic group having 2 to 20carbon atoms and more preferably a 5- or 6-membered heterocyclic grouphaving at least one oxygen atom, sulfur atom, or nitrogen atom), analkoxy group (preferably an alkoxy group having 1 to 20 carbon atoms),an aryloxy group (preferably an aryloxy group having 6 to 26 carbonatoms), an alkoxycarbonyl group (preferably an alkoxycarbonyl grouphaving 2 to 20 carbon atoms), an aryloxycarbonyl group (preferably anaryloxycarbonyl group having 6 to 26 carbon atoms), an amino group(preferably an amino group having 0 to 20 carbon atoms including analkylamino group and an arylamino group, such as amino,N,N-dimethylamino, N,N-diethylamino, N-ethylamino, and anilino), asulfamoyl group (preferably a sulfamoyl group having 0 to 20 carbonatoms), an acyl group (preferably an acyl group having 1 to 20 carbonatoms), an acyloxy group (preferably an acyloxy group having 1 to 20carbon atoms), a carbamoyl group (preferably a carbamoyl group having 1to 20 carbon atoms), an acylamino group (preferably an acylamino grouphaving 1 to 20 carbon atoms, such as an acetylamino group or abenzoylamino group), an alkylthio group (preferably an alkylthio grouphaving 1 to 20 carbon atoms), an arylthio group (preferably an arylthiogroup having 6 to 26 carbon atoms), an alkylsulfonyl group (preferablyan alkylsulfonyl group having 1 to 20 carbon atoms), an arylsulfonylgroup (preferably an arylsulfonyl group having 6 to 22 carbon atoms), analkylsilyl group (preferably an alkylsilyl group having 1 to 20 carbonatoms), an arylsilyl group (preferably an arylsilyl group having 6 to 42carbon atoms), an alkoxysilyl group (preferably an alkoxysilyl grouphaving 1 to 20 carbon atoms), an aryloxysilyl group (preferably anaryloxysilyl group having 6 to 42 carbon atoms), a phosphoryl group(preferably a phosphoryl group having 0 to 20 carbon atoms, for example,—OP(═O)(R^(P))₂), a phosphonyl group (preferably a phosphonyl grouphaving 0 to 20 carbon atoms, for example, —P(═O)(R^(P))₂), a phosphinylgroup (preferably a phosphinyl group having 0 to 20 carbon atoms, forexample, —P(R^(P))₂), a (meth)acryloyl group, a (meth)acryloyloxy group,a (meth)acryloylimino group (a (meth)acrylamide group), a hydroxylgroup, a thiol group, a carboxyl group, a phosphoric acid group, aphosphonic acid group, a sulfonic acid group, a cyano group, and ahalogen atom (for example, a fluorine atom, a chlorine atom, a bromineatom, an iodine atom, or the like). R^(P) represents a hydrogen atom, ahydroxyl group, or a substituent.

In addition, each of the groups exemplified as the substituent W may befurther substituted with the substituent W.

In a case where the aforementioned substituent is an acidic group or abasic group, the substituent may form a salt thereof.

In a case where the compound, the substituent, the linking group, andthe like contain an alkyl group, an alkylene group, an alkenyl group, analkenylene group, an alkynyl group, an alkynylene group, or the like,these may be cyclic or chainlike or may be linear or branched, and maybe substituted as described above or unsubstituted.

[Initiator]

It is preferable that the composition according to the embodiment of thepresent invention contains an initiator.

The initiator is not particularly limited, but is preferably a thermalpolymerization initiator or a photopolymerization initiator.

Examples of the photopolymerization initiator include analkylphenone-based photopolymerization initiator, a methoxyketone-basedphotopolymerization initiator, an acylphosphine oxide-basedphotopolymerization initiator, a hydroxyketone-based photopolymerizationinitiator (for example, IRGACURE184; 1,2-α-hydroxyalkylphenone), anaminoketone-based photopolymerization initiator (for example,2-methyl-1-[4-(methylthio)phenyl]-2-morpholino-propan-1-one (IRGACURE(registered trademark) 907)), an oxime-based photopolymerizationinitiator, and an oxyphenylacetic acid ester-based photopolymerizationinitiator (IRGACURE (registered trademark) 754), and the like.

Examples of other initiators include an azo-based polymerizationinitiator (for example, V-50 or V-601), a persulfate-basedpolymerization initiator, a persulfuric acid-based polymerizationinitiator, a redox-based polymerization initiator, and the like.

One kind of the initiator may be used singly, or two or more kinds ofthe initiators may be used in combination.

In the composition according to the embodiment of the present invention,the content of the initiator (total content in a case where thecomposition contains a plurality of kinds of initiators) is notparticularly limited. However, the content of the initiator with respectto the total solid content of the composition is preferably 0.5% to 10%by mass, and more preferably 1% to 5% by mass.

[Solvent]

It is preferable that the composition according to the embodiment of thepresent invention contains a solvent.

Examples of the solvent include water, an organic solvent (for example,esters such as ethyl acetate and n-butyl acetate; aromatic hydrocarbonssuch as toluene and benzene; aliphatic hydrocarbons such as n-hexane andn-heptane; alicyclic hydrocarbons such as cyclohexane andmethylcyclohexane; ketones such as methyl ethyl ketone (MEK), methylisobutyl ketone, and cyclohexanone; alcohols such as methanol andbutanol, or the like), and a mixed solvent of these.

Among these, from the viewpoint of making it difficult for surfaceunevenness to occur during coating, alcohol solvents such as methanoland ethanol are preferable.

One kind of the solvent may be used singly, or two or more kinds of thesolvents may be used in combination.

In the composition according to the embodiment of the present invention,the content of the solvent (total content in a case where thecomposition contains a plurality of kinds of solvents) with respect tothe total mass of the composition is preferably from 0.5% to 95% bymass, more preferably 1% to 90% by mass, and even more preferably 10% to80% by mass.

[Other Components]

The composition according to the embodiment of the present invention maycontain components other than the components described above. Examplesof such components include a binder resin, a polyfunctional amine, apolyfunctional thiol, a surfactant, a plasticizer, and a surfacelubricant, a leveling agent, a softener, an antioxidant, an antiagingagent, a light stabilizer, an ultraviolet absorber, an inorganic ororganic filler, a metal powder, and the like.

The binder resin is not particularly limited, and examples thereofinclude an acrylic resin, a styrene-based resin, a vinyl-based resin, apolyolefin-based resin, a polyester-based resin, a polyurethane-basedresin, a polyamide-based resin, a polycarbonate-based resin, apolydiene-based resin, an epoxy-based resin, a silicone-based resin, acellulose-based polymer, a chitosan-based polymer, and the like.

[Method for Preparing Curable Composition]

As the method for preparing the composition according to the embodimentof the present invention, a known method can be employed withoutparticular limitation. For example, the curable composition can beprepared by mixing together the above components and then stirring themixture by known means.

[Cured Product]

The cured product according to an embodiment of the present invention isformed by curing the aforementioned composition according to theembodiment of the present invention. The shape of the cured product canbe appropriately selected according to the use. Examples of the shape ofthe cured product include a powder shape and a film shape. Among these,a film shape is preferable.

In a case where the cured product is formed into a film, the filmthickness is not particularly limited, but is, for example, 0.1 to 300μm and more preferably 1 to 100 μm.

The cured product of the present invention contains a polymer compoundcontaining a repeating unit derived from the specific betaine monomerdescribed above.

[Method for Manufacturing Cured Product (Cured Film)]

The method for manufacturing the cured product (cured film) according tothe embodiment of the present invention is not particularly limited.Examples thereof include a method of coating a substrate with theaforementioned composition according to the embodiment of the presentinvention and then curing the composition by heating or lightirradiation (examples of the light include ultraviolet rays, visiblerays, X-rays, and the like).

The material of the substrate is not particularly limited, and examplesthereof include a metal material, a ceramic material, a plasticmaterial, and the like.

Examples of the type of the plastic material include polyethyleneterephthalate, polybutylene terephthalate, polyethylene naphthalate,polyethylene, polypropylene, cellophane, diacetyl cellulose, triacetylcellulose, acetyl cellulose butyrate, polyvinyl chloride, polyvinylidenechloride, polyvinyl alcohol, an ethylene-vinyl acetate copolymer,polystyrene, polycarbonate, polymethylpentene, polysulfone, polyetherether ketone, polyether sulfone, polyether imide, polyimide, afluororesin, nylon, an acrylic resin, polyamide, cycloolefin, polyethersulfan, and the like.

Examples of the type of the metal material include gold, stainlesssteel, a cobalt-chromium alloy, an amalgam alloy, a silver-palladiumalloy, a gold-silver-palladium alloy, titanium, a nickel-titanium alloy,platinum, and the like.

Examples of the type of the ceramic material include hydroxyapatite andthe like.

The shape of the substrate is not particularly limited, and may be aplate shape or a three-dimensional shape.

The method for coating the substrate with the composition of the presentinvention is not particularly limited, and examples thereof includemethods such as dipping, roll coating, kiss roll coating, gravurecoating, reverse coating, roll brush coating, spray coating, dip rollcoating, bar coating, spin coating, knife coating, air knife coating,curtain coating, lip coating, and an extrusion coating method using adie coater.

The heating method is not particularly limited, and examples thereofinclude a method using a blast dryer, an oven, an infrared dryer, aheating drum, and the like.

The heating temperature is not particularly limited, but is preferably30° C. to 150° C. and more preferably 40° C. to 120° C.

The heating time is not particularly limited, but is usually 1 minute to6 hours. In a case where the composition is dried in a coatingapparatus, the heating time is 1 to 20 minutes, and the heatingtemperature at the time of heating after the coating (for example,heating the substrate that is wound up) is preferably room temperatureto 50° C.

Examples of the method of light irradiation include methods using alow-pressure mercury lamp, a medium-pressure mercury lamp, ahigh-pressure mercury lamp, a metal halide lamp, a deep-UV (ultraviolet)light, an LED (light emitting diode), a xenon lamp, a chemical lamp, acarbon arc lamp, and the like. The energy of light irradiation is notparticularly limited, but is preferably 0.1 to 10 J/cm².

<Use>

The cured product according to the embodiment of the present inventionexhibits excellent substrate adhesion and can inhibit or prevent theadhesion of biological materials such as cells and blood components. Thecured product of the present invention can be suitably used forprostheses, medical instruments, and the like as a material applied to aliving body (biomaterial). Specifically, the cured product according tothe embodiment of the present invention may be used as a filler for aresin composition used as a material for a prosthesis, a medicalinstrument, and the like, or may be used as a coating material by beingdisposed on the surface of a prosthesis or a medical instrument.Examples of the medical instrument include a denture, an artificialdialysis membrane, a catheter, and the like. The prosthesis refers to amember that is incorporated into the human body for a long-termtreatment or the like, and examples thereof include an artificial bloodvessel, a stent, an artificial organ, an artificial bone, an artificialvalve, cultured skin, and the like.

The cured product according to the embodiment of the present inventionis particularly preferably used as a dental material or an artificialbone adhesive.

[Medical Member]

The medical member according to an embodiment of the present inventionincludes a substrate and a cured product disposed on the substrate.

The substrate means the aforementioned prosthesis, medical instrument,and the like, and examples thereof include those made of the metalmaterial, the ceramic material, and the plastic material describedabove. Specifically, examples of the substrate include dentures andartificial bones.

The cured film corresponds, for example, to the aforementioned curedproduct having a film shape.

EXAMPLES

Hereinafter, the present invention will be more specifically describedbased on examples. The materials, the amount and ratio thereof used, howto treat the materials, the treatment procedure, and the like describedin the following examples can be appropriately changed as long as thegist of the present invention is maintained. Therefore, the scope of thepresent invention is not limited to the following examples.

[Preparation of Curable Composition]

[Various Components]

<Specific Betaine Monomer>

The specific betaine monomers (ex (1) to ex (6)) shown in Table 1 willbe shown below.

(Synthesis of Ex (1))

Hereinafter, the method for synthesizing the specific betaine monomersex (1), ex (2), ex (5), and ex (6) will be explained by describing themethod for synthesizing ex (1) for example.

3-(Dimethylamino)-1,2-propanediol (10 g, 83.9 mmol) and tetrahydrofuran(THF, 50 mL) were mixed together, and a solution which was obtained bydiluting 2-isocyanatoethyl methacrylate (27.34 g, 176 mmol) withtetrahydrofuran (50 mL) was added dropwise to the mixture. Furthermore,a solution obtained by diluting “NEOSTAN U600” (manufactured by NITTOKASEI CO., LTD., 538 mg) with tetrahydrofuran (10 mL) was added dropwiseto the above solution while paying attention to heat generation, and themixture was stirred at room temperature for 12 hours. The reactionsolution was concentrated under reduced pressure, and the obtained crudeproduct was purified by silica gel column chromatography (eluent: ethylacetate to ethyl acetate:methanol=4:1), thereby obtaining anintermediate a (30 g, yield 83%).

The intermediate a (5 g, 11.6 mmol), 1,4-butanesultone (1.9 g, 14.0mmol), 4-hydroxy-2,2,6,6-tetramethylpiperidine 1-oxyl free radical (60mg, 0.35 mmol), and methanol (6 mL) were mixed together and stirred at80° C. for 48 hours. The reaction solution was cooled to roomtemperature and concentrated under reduced pressure. The obtained crudeproduct was purified by silica gel column chromatography (eluent:acetone to acetone:methanol=1:1 to methanol), thereby obtaining ex (1)(5 g, yield 76%). Through ¹H NMR (Nuclear Magnetic Resonance), it wasconfirmed that the obtained product was a target sub stance.

¹H NMR (methanol-d₄, 400 MHz) δ: 1.82 (2H, t), 1.93 (6H, s), 1.93-2.09(2H, m), 2.88 (2H, t), 3.15 (6H, s), 3.34-3.44 (6H, m), 3.57-3.78 (2H,m), 4.08-4.30 (6H, m), 5.63 (2H, s), 6.12 (2H, s).

Furthermore, by ESI-MS (Electrospray Ionization-Mass Spectrometry), apeak corresponding to the molecular weight of the target substance wasconfirmed.

(Synthesis of Ex (2), Ex (5), and Ex (6))

ex (2), ex (5), and ex (6) were synthesized according to the method forsynthesizing ex (1).

(Synthesis of Ex (3))

ex (3) was synthesized according to the method described in polymer 52(2011) 3011-3020.

(Synthesis of Ex (4))

ex (4) was synthesized according to the method described in Chem.Commun., 2015, 51, 183-186.

<Specific Polyfunctional (Meth)Acrylamide Compound>

Specific polyfunctional (meth)acrylamide compounds (C (1) to C (4))shown in Table 1 will be shown below.

<Comparative Betaine Monomer>

A comparative betaine monomer (Com (1)) shown in Table 1 will be shownbelow.

<Comparative Copolymerized Monomer>

Comparative copolymerized monomers (Com (2) and Com (3)) shown in Table1 will be shown below.

[Preparation of Curable Composition]

The components shown in the following Table 1 were dissolved in asolvent (methanol), thereby preparing curable compositions having aconcentration of solid contents of 20% by mass (curable compositions 1to 29). Regarding the curable compositions, the solid contents mean allcomponents except for the solvent.

The numerical value in Table 1 represents the content (% by mass) ofeach component with respect to the total solid content of a curablecomposition. “Irg2959” corresponds to a polymerization initiator(“IRGACURE 2959”, manufactured by BASF SE).

[Preparation of Film]

<Preparation of Coat Film for Evaluating Substrate Adhesion andBiocompatibility>

By using a spin coater, a substrate (acrylic plate (manufacturer: MISUMICorporation, model number: ACA)) was coated with each of the preparedcurable compositions such that the film thickness became about 5 μm, andthen the composition was dried. Then, by using an “ECS-401G (tradename)” UV (ultraviolet) exposure machine (light source: high-pressuremercury lamp) manufactured by EYE GRAPHICS Co., Ltd., the compositionwas exposed at an exposure amount of 4 J/cm², thereby preparing a coatfilm for evaluating substrate adhesion and biocompatibility.

[Evaluation]

<Substrate Adhesion Test>

The prepared acrylic plate with a coat film was immersed in a PBS(Phosphate buffered saline) solution at 37° C. for 48 hours. Thereafter,the acrylic plate with a coat film was pulled up from the solution, andthe substrate adhesion was evaluated based on the area of the coat filmremaining on the acrylic plate (hereinafter, referred to as “residualcoat film” as well). The area of the residual coat film with respect tothe area of the acrylic plate was expressed as a percentage as a coatingrate, and evaluated based on the following evaluation standard.Regarding the evaluation of the substrate adhesion, samples graded “B”or higher were regarded as acceptable. The results are shown in Table 1.

(Evaluation Standard)

“A”: The coating rate was equal to or higher than 90%.

“B”: The coating rate was equal to or higher than 70% and less than 90%.

“C”: The coating rate was equal to or higher than 50% and less than 70%.

“D”: The coating rate was less than 50%.

<Evaluation of Biocompatibility (Cell Adhesion Test)>

The prepared acrylic substrate with a coat film was placed in a 6-wellplate, and mouse-derived fibroblasts (3T3 cells) were dispersed inDulbecco's modified Eagle medium at a seeding density of 1.0×10⁵cells/cm². By using an incubator, the cells were cultured for 48 hoursunder the condition of 37° C. and 5% carbon dioxide.

Thereafter, the acrylic substrate with the coat film was taken outobserved using a phase contrast microscope (an inverted cubic researchmicroscope, manufactured by Olympus Corporation) so as to check whetheror not the cells were attached thereto. The magnification was 4×.

This operation was performed on 10 acrylic substrates with a coat film,and biocompatibility was evaluated as below based on the number ofacrylic substrates with a coat film to which cells had adhered.Regarding the evaluation of the biocompatibility, samples graded “C” orhigher were regarded as acceptable. For practical use, samples graded“B” or higher are preferable. The results are shown in Table 1.

In addition, “-” shown in the column of Biocompatibility in Table 1means that the sample could not be evaluated because the film was peeledoff.

(Evaluation Standard)

“A”: 0 to 3

“B”: 4 to 6

“C”: 7 to 9

“D”: 10 or greater

TABLE 1 Makeup of curable composition Component A Component B Curablecomposition No. Type Note Type Example 1 Curable composition 1 ex (1)(67%) Corresponding to Formula (1)/sulfobetaine C (3) (30%) Example 2Curable composition 2 ex (2) (67%) Corresponding to Formula(2)/sulfobetaine C (3) (30%) Example 3 Curable composition 3 ex (3)(67%) Corresponding to Formula (2)/sulfobetaine C (3) (30%) Example 4Curable composition 4 ex (4) (67%) Corresponding to Formula(2)/sulfobetaine C (3) (30%) Example 5 Curable composition 5 ex (5)(67%) Corresponding to Formula (2)/sulfobetaine C (3) (30%) Example 6Curable composition 6 ex (6) (67%) Corresponding to Formula(2)/carboxybetaine C (3) (30%) Example 7 Curable composition 7 ex (1)(67%) Corresponding to Formula (1)/sulfobetaine C (1) (30%) Example 8Curable composition 8 ex (2) (67%) Corresponding to Formula(2)/sulfobetaine C (1) (30%) Example 9 Curable composition 9 ex (3)(67%) Corresponding to Formula (2)/sulfobetaine C (1) (30%) Example 10Curable composition 10 ex (4) (67%) Corresponding to Formula(2)/sulfobetaine C (1) (30%) Example 11 Curable composition 11 ex (5)(67%) Corresponding to Formula (2)/sulfobetaine C (1) (30%) Example 12Curable composition 12 ex (6) (67%) Corresponding to Formula(2)/carboxybetaine C (1) (30%) Example 13 Curable composition 13 ex (1)(67%) Corresponding to Formula (l)/sulfobetaine C (4) (30%) Example 14Curable composition 14 ex (2) (67%) Corresponding to Formula(2)/sulfobetaine C (4) (30%) Example 15 Curable composition 15 ex (3)(67%) Corresponding to Formula (2)/sulfobetaine C (4) (30%) Example 16Curable composition 16 ex (4) (67%) Corresponding to Formula(2)/sulfobetaine C (4) (30%) Example 17 Curable composition 17 ex (5)(67%) Corresponding to Formula (2)/sulfobetaine C (4) (30%) Example 18Curable composition 18 ex (6) (67%) Corresponding to Formula(2)/carboxybetaine C (4) (30%) Comparative Example 1 Curable composition19 ex (3) (97%) Corresponding to Formula (2)/sulfobetaine — ComparativeExample 2 Curable composition 20 ex (4) (97%) Corresponding to Formula(2)/sulfobetaine — Comparative Example 3 Curable composition 21 com (1)(97%) — — Comparative Example 4 Curable composition 22 com (1) (67%) — C(1) (30%) Comparative Example 5 Curable composition 23 com (1) (67%) — C(2) (30%) Comparative Example 6 Curable composition 24 com (1) (67%) — C(3) (30%) Comparative Example 7 Curable composition 25 com (1) (67%) — C(4) (30%) Comparative Example 8 Curable composition 26 ex (3) (67%)Corresponding to Formula (2)/sulfobetaine Com (2) (30%) ComparativeExample 9 Curable composition 27 ex (3) (67%) Corresponding to Formula(2)/sulfobetaine Com (3) (30%) Comparative Example 10 Curablecomposition 28 ex (4) (67%) Corresponding to Formula (2)/sulfobetaineCom (2) (30%) Comparative Example 11 Curable composition 29 ex (4) (67%)Corresponding to Formula (2)/sulfobetaine Com (3) (30%) Makeup ofcurable composition Evaluation result Component B Substrate NotePolymerization initiator adhesion Biocompatibility Example 1Corresponding to Formula (A2)/Formula (A3) Irg2959 (3%) A A Example 2Corresponding to Formula (A2)/Formula (A3) Irg2959 (3%) A A Example 3Corresponding to Formula (A2)/Formula (A3) Irg2959 (3%) B A Example 4Corresponding to Formula (A2)/Formula (A3) Irg2959 (3%) B A Example 5Corresponding to Formula (A2)/Formula (A3) Irg2959 (3%) A A Example 6Corresponding to Formula (A2)/Formula (A3) Irg2959 (3%) A B Example 7Corresponding to Formula (A1) Irg2959 (3%) A B Example 8 Correspondingto Formula (A1) Irg2959 (3%) A B Example 9 Corresponding to Formula (A1)Irg2959 (3%) B B Example 10 Corresponding to Formula (A1) Irg2959 (3%) BB Example 11 Corresponding to Formula (A1) Irg2959 (3%) A B Example 12Corresponding to Formula (A1) Irg2959 (3%) A C Example 13 Correspondingto Formula (A2) Irg2959 (3%) A B Example 14 Corresponding to Formula(A2) Irg2959 (3%) A B Example 15 Corresponding to Formula (A2) Irg2959(3%) B B Example 16 Corresponding to Formula (A2) Irg2959 (3%) B BExample 17 Corresponding to Formula (A2) Irg2959 (a %) A B Example 18Corresponding to Formula (A2) Irg2959 (3%) A C Comparative Example 1 —Irg2959 (3%) C A Comparative Example 2 — Irg2959 (3%) C A ComparativeExample 3 — Irg2959 (3%) D — Comparative Example 4 Corresponding toFormula (A1) Irg2959 (3%) D — Comparative Example 5 Corresponding toFormula (A2) Ire2959 (3%) D — Comparative Example 6 Corresponding toFormula (A2)/Formula (A3) Irg2959 (3%) D — Comparative Example 7Corresponding to Formula (A2) Irg2959 (3%) D — Comparative Example 8 —Irg2959 (3%) B D Comparative Example 9 — Irg2959 (3%) B D ComparativeExample 10 — Irg2959 (3%) B D Comparative Example 11 — Irg2959 (3%) B D

From the results in Table 1, it was confirmed that according to thecurable compositions of Examples, a cured product having excellentsubstrate adhesion and excellent biocompatibility was obtained.

By the comparison of Examples 1, 2, and 6, it was confirmed that in acase where A¹ in the compound represented by Formula (1) and A² in thecompound represented by Formula (2) each represented S═O (that is, in acase where the compounds had a sulfobetaine structure), thebiocompatibility was further improved.

By the comparison of Examples 1 to 18, it was confirmed thatparticularly, in a case where the compound represented by Formula (A3)among the compounds represented by Formula (A2) was used as the specificpolyfunctional (meth)acrylamide compound, the substrate adhesion and thebiocompatibility were further improved.

On the other hand, it was confirmed that the cured product obtained fromthe curable composition of the comparative example did not satisfy thedesired requirements.

What is claimed is:
 1. A curable composition comprising: one or morebetaine monomers selected from the group consisting of a compoundrepresented by Formula (1) and a compound represented by Formula (2);and one or more polyfunctional compounds selected from the groupconsisting of a compound represented by Formula (A1) and a compoundrepresented by Formula (A2),

in the formula, R¹ represents a hydrogen atom or an alkyl group, R² andR³ each independently represent an alkyl group, R^(1A) represents anoxygen atom or NR^(101,) R¹⁰¹ represents a hydrogen atom or an alkylgroup, a represents an integer of 2 to 6, L¹ represents an (a+1)-valentaliphatic hydrocarbon group which may contain —O—, —NR¹⁰²-, —CO—, or adivalent linking group obtained by combining these, L² represents adivalent aliphatic hydrocarbon group which may contain —O—, —NR¹⁰²-,—CO—, or a divalent linking group obtained by combining these, A¹represents S═O or a carbon atom, R¹⁰² represents a hydrogen atom or asubstituent,

in the formula, R⁴ and R⁶ each independently represent a hydrogen atomor an alkyl group, R⁵ represents an alkyl group, R^(1B) and R^(1C) eachindependently represent an oxygen atom or NR¹⁰³, R¹⁰³ represents ahydrogen atom or an alkyl group, b and c each independently represent aninteger of 1 to 5, b and c satisfy 2≤b+c≤6, L³ represents a (b+1)-valentaliphatic hydrocarbon group which may contain —O—, —NR¹⁰⁴-, —CO—, or adivalent linking group obtained by combining these, L⁴ represents a(c+1)-valent aliphatic hydrocarbon group which may contain —O—, —NR¹⁰⁴-,—CO—, or a divalent linking group obtained by combining these, L⁵represents a divalent aliphatic hydrocarbon group which may contain —O—,—NR¹⁰⁴-, —CO—, or a divalent linking group obtained by combining these,R¹⁰⁴ represents a hydrogen atom or a substituent, A² represents S═O or acarbon atom,

in Formula (A1), R²⁰ each independently represents a hydrogen atom or amethyl group, L²⁰ each independently represents —O—, an alkylene grouphaving 2 to 4 carbon atoms, or a divalent linking group obtained bycombining these, a plurality of R²⁰s may be the same as or differentfrom each other, in Formula (A2), R²⁰ each independently represents ahydrogen atom or a methyl group, R²¹ and R²³ each independentlyrepresent —O—, an alkylene group having 1 to 4 carbon atoms, or adivalent linking group obtained by combining these, R²² represents —O—,an alkylene group having 1 to 4 carbon atoms, a group represented byFormula (B), or a divalent linking group obtained by combining these,L²¹ and L²² each independently represent a single bond or a grouprepresented by Formula (B), in Formula (B), R²⁰ represents a hydrogenatom or a methyl group, and * represents a binding position.
 2. Thecurable composition according to claim 1, wherein A¹ in Formula (1)represents S═O, and A² in Formula (2) represents S═O.
 3. A filmcomprising: a polymer compound containing one or more repeating unitsselected from the group consisting of a repeating unit derived from acompound represented by Formula (1) and a repeating unit derived from acompound represented by Formula (2), and one or more repeating unitsselected from the group consisting of a repeating unit derived from acompound represented by Formula (A1) and a repeating unit derived from acompound represented by Formula (A2),

in the formula, R¹ represents a hydrogen atom or an alkyl group, R² andR³ each independently represent an alkyl group, R^(1A) represents anoxygen atom or NR^(101,) R¹⁰¹ represents a hydrogen atom or an alkylgroup, a represents an integer of 2 to 6, L¹ represents an (a+1)-valentaliphatic hydrocarbon group which may contain —O—, —NR¹⁰²-, —CO—, or adivalent linking group obtained by combining these, L² represents adivalent aliphatic hydrocarbon group which may contain —O—, —NR¹⁰²-,—CO—, or a divalent linking group obtained by combining these, A¹represents S═O or a carbon atom, R¹⁰² represents a hydrogen atom or asubstituent,

in the formula, R⁴ and R⁶ each independently represent a hydrogen atomor an alkyl group, R⁵ represents an alkyl group, R^(1B) and R^(1C) eachindependently represent an oxygen atom or NR¹⁰³, R¹⁰³ represents ahydrogen atom or an alkyl group, b and c each independently represent aninteger of 1 to 5, b and c satisfy 2≤b+c≤6, L³ represents a (b+1)-valentaliphatic hydrocarbon group which may contain —O—, —NR¹⁰⁴-, —CO—, or adivalent linking group obtained by combining these, L⁴ represents a(c+1)-valent aliphatic hydrocarbon group which may contain —O—, —NR¹⁰⁴-,—CO—, or a divalent linking group obtained by combining these, L⁵represents a divalent aliphatic hydrocarbon group which may contain —O—,—NR¹⁰⁴-, —CO—, or a divalent linking group obtained by combining these,R¹⁰⁴ represents a hydrogen atom or a substituent, A² represents S═O or acarbon atom,

in Formula (A1), R²⁰ each independently represents a hydrogen atom or amethyl group, L²⁰ each independently represents —O—, an alkylene grouphaving 2 to 4 carbon atoms, or a divalent linking group obtained bycombining these, a plurality of R²⁰s may be the same as or differentfrom each other, in Formula (A2), R²⁰ each independently represents ahydrogen atom or a methyl group, R²¹ and R²³ each independentlyrepresent —O—, an alkylene group having 1 to 4 carbon atoms, or adivalent linking group obtained by combining these, R²² represents —O—,an alkylene group having 1 to 4 carbon atoms, a group represented byFormula (B), or a divalent linking group obtained by combining these,L²¹ and L²² each independently represent a single bond or a grouprepresented by Formula (B), in Formula (B), R²⁰ represents a hydrogenatom or a methyl group, and * represents a binding position.
 4. A curedproduct formed by curing the curable composition according to claim 1.5. The cured product according to claim 4 that is a film.
 6. The curedproduct according to claim 4 that is used as a filler for a resincomposition, a material for a prosthesis, a medical instrument, or acoating material by being disposed on the surface of a prosthesis or amedical instrument.
 7. A medical member comprising: a substrate; and thecured product according to claim 4 disposed on the substrate.